Synthesis and characterization of naphthoxazine functional poly(ε-caprolactone)

Kışkan, Barış; Yaǧcı, Yusuf

doi:10.1016/j.polymer.2005.09.061

Cited by 100 publications

(66 citation statements)

References 26 publications

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“…In this connection, it should be pointed out that a P-a-functionalized poly(ecaprolactone) also does not exhibit exotherms that are observed with low-molecular-weight P-as. [20] Therefore, the thermal curability of the benzoaxazine groups is indirectly demonstrated. For this purpose the bisbenzoxazine (B-a) with the structure shown in Figure 5 has been cured by heating at 200 8C for 1 h in the presence of PMMA/ P-a.…”

Section: Resultsmentioning

confidence: 99%

“…[18] We have recently reported several routes to incorporate these interesting P-a structures into polymer chains. [19][20][21] As part of our continuing interest in alternative photoinitiating systems, we now report the use of P-a as a hydrogen donor in conjunction with aromatic carbonyl photosensitizers in a photoinitiated free radical polymerization.…”

Section: Introductionmentioning

confidence: 99%

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Photoinitiated Free Radical Polymerization Using Benzoxazines as Hydrogen Donors

Taşdelen

Kışkan

Yaǧcı

2006

Macromol. Rapid Commun.

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Summary: Free radical polymerization of methyl methacrylate (MMA) is initiated upon irradiation at λ > 350 nm in CH2Cl2 that contains benzoxazine (P‐a) and one of the following photosensitizers: benzophenone (BP), thioxanthone (TX), 2‐chlorothioxanthone (CTX), 2‐isopropyl thioxanthone (ITX), and camphorquinone (CQ). The postulated mechanism is based on the intermolecular reaction of the excited photosensitizer with the tertiary amino moiety of the ground state P‐a and a subsequent hydrogen abstraction reaction. The resulting aminoalkyl radicals initiate the polymerization. The incorporation of P‐a groups into polymers is demonstrated by spectroscopic methods. The possibility of deep curing using the described photoinitiating system followed by the thermal ring opening of the incorporated P‐a groups is also demonstrated.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Photoinitiated Free Radical Polymerization Using Benzoxazines as Hydrogen Donors

Taşdelen

Kışkan

Yaǧcı

2006

Macromol. Rapid Commun.

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“…This methodology affords possibility to incorporate functional groups into polyesters provided that in addition to the hydroxyl groups, the initiator contains desired functionality. Previously, we have prepared thermal- [21][22][23][24][25][26][27], photo- [28,29], and electro-functional [30] polymers of biocompatible polymers by taking advantage of the functional initiator approach [31].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and hydrolytic degradation of graft copolymers of polystyrene and aliphatic polyesters

Küküt

Karal-Yılmaz

Yaǧcı

2012

Designed Monomers and Polymers

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In the present study, a new class of biodegradable graft copolymers of polystyrene (PS) with aliphatic polyester (APE) side chains were synthesized through combination of nitroxide-mediated free radical polymerization (NMRP) and ringopening polymerization (ROP) with copper (I)-catalyzed 'click' chemistry. First, the click component, azido-functional PS (PS-N 3 ) was prepared by copolymerization of styrene and chloromethyl styrene by NMRP followed by the conversion of chlorine groups of the resulting copolymer to azido groups by using NaN 3 in N,N-dimethylformamide. Propargyl functional APEs were prepared independently by ROP of lactic acid and glycolic acid using tin octoate in the presence of propargyl alcohol at 130°C. Finally, PS-N 3 was coupled with the resulting polymers by click chemistry to yield graft copolymers (PS-g-poly (L-lactic-co-glycolic acid) [PLLA] and PS-g-PLLGA, respectively). The intermediates and final graft copolymers were characterized by proton nuclear magnetic resonance ( 1 H NMR) and Fourier transform infrared spectral and gel permeation chromatography analyses. The hydrolytic degradation behavior of the obtained graft copolymers in phosphate buffer saline solution were investigated by the weight loss and molecular weight measurements. It is shown that both copolymers undergo slow hydrolytic degradation, PS-g-PGLLA being relatively faster due to the presence of hydrophilic glycolic acid groups in the structure.

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“…[4,5] Therefore, several strategies have been developed to overcome the associated disadvantages of benzoxazine resins, such as (i) preparation of modified monomers with additional functionality, (ii) synthesis of novel polymeric benzoxazine precursors, and (iii) blending with highperformance polymers or fillers and fibers. [6,7] In recent years, much works have been devoted to the synthesis of novel polymeric-based precursors by incorporating benzoxazine units either as side chain [8][9][10][11][12][13][14] or as chain-end [15][16][17][18][19] or in main chain. [20][21][22][23][24][25][26][27][28][29][30][31][32][33][34] There are many examples of the polymeric benzoxazine precursors from commercially important polymers such as polystyrene, [11,13,17] poly(methyl methacrylate), [16] poly(e-caprolactone), [15] poly(vinyl chloride), [10] poly( p-vinylphenol), [14] polyacetylene, [9] polysiloxane, [29][30][31] polyether, [18,…”

Section: Introductionmentioning

confidence: 99%

Thermally Curable Polyoxanorbornene by Ring Opening Metathesis Polymerization

Taşdelen

Durmaz

2011

Macro Chemistry & Physics

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A novel norbornene monomer bearing a thermally curable benzoxazine group is synthesized and polymerized by ROMP using the Grubbs first‐generation ruthenium catalyst. The $\overline {M} _{{\rm w}} $ of the side‐chain benzoxazine functionalized polyoxanorbornene can be up to 87 000 Da with unimodal molecular‐weight distribution and narrow polydispersity between 1.18 and 1.65. Thermally activated ring‐opening polymerization of benzoxazine moieties leads to the formation of highly cross‐linked structures. The effects of molecular weight on the thermal ROP of polybenzoxazine precursors are examined.magnified image

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Synthesis and characterization of naphthoxazine functional poly(ε-caprolactone)

Cited by 100 publications

References 26 publications

Photoinitiated Free Radical Polymerization Using Benzoxazines as Hydrogen Donors

Photoinitiated Free Radical Polymerization Using Benzoxazines as Hydrogen Donors

Synthesis, characterization, and hydrolytic degradation of graft copolymers of polystyrene and aliphatic polyesters

Thermally Curable Polyoxanorbornene by Ring Opening Metathesis Polymerization

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